A novel one-pot synthesis of substituted 4-t-butyldimethylsilyloxy-thiazoles |
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Institution: | 1. School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001, China;2. Henan Key laboratory for Pharmacology of Liver Disease, Academy of Medical and Pharmaceutical Science, Zhengzhou University, Zhengzhou 450052, China;3. School of Pharmaceutical Science, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, China;1. Department of Pure and Applied Sciences, Chemistry Section, University of Urbino “Carlo Bo”, P.zza Rinascimento 6, I-61029 Urbino, Italy;2. Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, P.zza Rinascimento 6, I-61029 Urbino, Italy;1. Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P.04510, México CDMX, Mexico;2. Instituto de Fisiología Celular, Universidad Nacional Autónoma de México, Cd. Universitaria, México CDMX, Mexico;3. Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, C.P. 04510, México CDMX, Mexico;1. Kosterlitz Centre for Therapeutics, Institute of Medical Sciences, University of Aberdeen, Foresterhill AB25 2ZD, Scotland, UK;2. Neuroscienze PharmaNess Scarl, Parco Scientifico della Sardegna, Edificio 5, Loc. Piscinamanna, 09010 Pula, CA, Italy;3. KemoTech s.r.l., Parco Scientifico della Sardegna, Edificio 3, Loc. Piscinamanna, 09010 Pula, CA, Italy;4. C.N.R.-I.C.R.M., via Mancinelli 7, 20131 Milano, Italy |
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Abstract: | The reaction of 2-halo-acylimidazolides or halides with primary thioamides in base give 2-halo-N-acylthioamides, which cyclize to the substituted 4-thiazolones and are trapped as the novel 4-t-butyldimethylsilyloxythiazoles in fair to good yield. The 2-aryl-4-t-butyldimethylsilyloxythiazoles undergo a 4+2] cycloaddition reaction with dimethoxyacetylene dicarboxylate DMAD] to give substituted 2-pyridones in fair yield. |
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